


Office Hours with Professor Winchester

by DeansDirtyLittleSecret



Series: Professor Dean Winchester AU [2]
Category: Supernatural
Genre: Alternate Universe - College/University, Explicit Language, Explicit Sexual Content, F/M, Oral Sex, Originally Posted on Tumblr, Professor Dean Winchester, Reader-Insert, Smut
Language: English
Status: Completed
Published: 2015-07-17
Updated: 2015-07-17
Packaged: 2018-04-09 20:49:38
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,295
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4363685
Author URL: https://archiveofourown.org/users/DeansDirtyLittleSecret/pseuds/DeansDirtyLittleSecret
Summary: <blockquote class="userstuff">
              <p>Reader has gotten involved in a relationship (of sorts) with her college history professor, Dean Winchester.</p>
            </blockquote>





	Office Hours with Professor Winchester

**Author's Note:**

> This is a professor!Dean AU. Reader is in her last year of college and just a few years younger than Dean.

Jo dropped her books to the table next to you, pulling you from your very vivid daydream about Professor Winchester and his lips. You jumped and sat up, forcing yourself not to snap at her in irritation.

“Hey, did you turn in that application yet?” she asked, dropping into the chair across from you.

“What application?” you asked, confused.

“The one for Professor Winchester?” Jo explained. “To be his teaching assistant? It was literally all you could talk about last week.”

“Yeah, yeah,” you said. “I forgot about that.” You’d had a few other things on your mind. Like the illicit relationship you were apparently now having with your new professor.

“Well, you better get on it,” Jo said. “I know of a couple people who are interested in it. Actually, a lot of people. I mean, have you seen him?”

“Um, yeah, I’ve seen him,” you nodded. You’d seen more of Professor Winchester than you’d ever imagined you would.

“God, he’s gorgeous, isn’t he?” Jo laughed. “He and Sam have been friends since college, though I’d never met him, not until he came to the party. I tried to get Sam to hook us up, but I guess when he talked to him about it, he said he’s involved with someone. Wouldn’t say who, though. Probably some girl at the university he was teaching at overseas.”

You felt a hard knot of jealousy forming in the pit of your stomach - over Jo and her interest in Dean and over the potential of there being someone else in his life. This conversation was not helping the insecurities you were already feeling about yourself and your handsome professor. You’d barely had a chance to talk to him since that first day in class, let alone see him. You’d only managed to exchange a few text messages filled with promises to see each other as soon as possible. That had been a week ago.

You closed your eyes and took a deep breath. “When did Sam talk to him?” you finally managed to ask.

“Um, last night, I think,” Jo said. She stole a couple of fries from the plate next to your elbow. “Why?”

“Just curious,” you mumbled. You gathered your books, shoving them into your bag. “Look, I have to go.”

Jo looked at you curiously, obviously confused by your behavior. “Um, okay,” she said. “Do you want some company?”

“No, no,” you sputtered. “I’m good.”

You had less than an hour before Dean’s class, but you wanted to talk to him, get some stuff out in the open. You’d jumped into this - whatever it was - feet first and blindfolded. You’d been hasty, entranced by the charm of the handsome professor and the attention he’d given you. For all you knew, he did have a girlfriend. You needed answered immediately.

You hurried across campus, the heat beating down on you. Dean’s syllabus had said he had office hours for an hour right before each class, so you were sure you could catch him, hopefully alone. You just wanted a few minutes to clear some stuff up. The air conditioning hit you in the face as soon as you opened the building door, goosebumps covering your skin. You shivered slightly at the sudden change in temperature. Dean’s class was at the back of the building, so you hurried down the hallway, the sounds of lecturing professors filtering out of the various classrooms.

When you finally arrived at Dean’s classroom, you opened the door just a fraction of an inch, not wanting to interrupt him if he was with another student. The classroom was dark, but there was a light on in his office. You looked over your shoulder before stepping inside, making sure the door closed behind you.

You stopped outside the office door and glanced inside. Dean was reclining on his ugly plaid couch, his legs stretched out in front of him, crossed at the ankles, a pen in his mouth, a stack of papers in his hand. There was a burger and a large soda on the table at the end of the couch, but it was untouched. He must have been running his fingers through his hair because it was messy, sticking up in several places. The radio was on, classic rock coming from the speakers. You tapped lightly on the doorjamb.

He looked up, a smile lighting up his face when he saw you, the pen still in his mouth. He gestured for you to come in, then he picked up a remote sitting beside his leg and turned down the radio. He dropped the pen and papers to the floor by his feet as he sat up.

“This is a nice surprise,” he said. “What’s up?”

“I thought we needed to talk,” you said, still standing just outside the door.

“Okay,” Dean muttered, dragging out the word. “You know that never sounds good, right?”

“I know,” you answered. You ran your hands through your hair, not quite sure how to proceed or if you even wanted to anymore. You looked over your shoulder again, stepped inside the office and pushed the door closed. You didn’t step any further into the room, instead you leaned against the door, arms crossed.

“What’s wrong?” Dean asked, rising to his feet.

“Do you have a girlfriend?” you blurted.

Dean looked at the floor, a slight smile on his face, shaking his head. “Is that what this about?” he asked. “You think I have a girlfriend?”

“Jo said...well, she said that Sam told her you were involved with someone,” you said. You shrugged, suddenly uncomfortable.

He crossed the room in two long strides to stand in front of you. He put a hand on either side of your head, his white shirtsleeves stark against his tanned skin. “I don’t have a girlfriend,” he murmured. “I told Sam that because I don’t want to date his sister. But I couldn’t exactly say that I’m dating a student, either.” He dropped his hands and shoved them into the pockets of his dark gray dress pants. “Look, Y/N, this...thing...between you and I, it’s...it could get complicated. You are a student, one of my students. We have to, well, we have to be careful. I could lose my job.”

“I know,” you replied with a sigh. “I understand if...you know, you don’t want to see me. I promise I won’t cause a problem or anything. Once I graduate…”

“Y/N, stop,” Dean interrupted. “I want to see you now, not when the year is over.” He reached out and took your hand. “But only if you’re comfortable with it. If you’re not okay with us keeping it quiet, then I understand. No hard feelings.” The look on his face was honest and very earnest, but also a little bit sad.

You didn’t want to end things, not in a million years. Dean had ignited something in you - he made you feel alive, beautiful, wanted. You weren’t ready or willing to walk away from that. You tightened your grip on his hand and took a step closer to him.

“We’ll figure it out,” you murmured. “I don’t want to give this up either, whatever this is.”

When Dean smiled, it lit up his entire face. He had these gorgeous little crinkles at the corner of his eyes and the green sparkled like dewy grass hit by morning sunlight. “Yeah?” he whispered.

“Yeah,” you smiled back. You took a hold of his navy blue tie, wrapping it around your hand and giving it a gentle tug. “I like your tie, Professor Winchester.”

“I love it when you call me that,” he said. Dean leaned over you, his lips just inches from yours. They brushed over yours, soft and gentle, just a light kiss, but heat immediately pooled in the pit of your stomach. His arm slid around your waist, pulling you tight against him. You could feel the thump of his heart beneath the hand pressed to his chest.

“I’ve wanted to do that for a week,” he growled. “I’ve been watching you during class, the way you chew on your pen, or how you smile when I say something funny, or how you cross your ankles so demurely. You’re killing me, Y/N. You can’t even begin to imagine the things I think about doing to you.” Both of his hands dropped to your ass, pulling you tight against him, his tongue sliding past your lips and into your mouth. He backed up, pulling you with him, until he was leaning against his desk and you were standing between his legs, your body flush against his.

You could feel his arousal through the cotton fabric of his dress pants, pressing into your stomach. You moaned, released his tie and slid your hand down his chest and over his stomach, grasping him through his pants and stroking him gently. His hips moved minutely, a tiny gasp escaping him.

When you moved to unbutton his pants, Dean caught your wrist in his hand. He broke off the kiss and sighed, his forehead resting against yours. “Class starts in ten minutes,” he groaned.

“Damn,” you muttered.

“Stay after?” he asked.

“Yes,” you nodded. You had a feeling the next hour and a half was going to be the longest of your life.

* * *

You and Dean managed to get yourselves somewhat put back together before your class started, though Professor Winchester had a decidedly pink blush to his cheeks and a low growl in his throat during the first few minutes. You had to force yourself to look anywhere but at him, because that just made you want to vault across the desks and rip his clothes off of him. You kept your head down, madly scribbling notes in the margins of your book.

Fortunately, Dean was a good teacher, keeping his class lighthearted, even funny, and interesting. You quickly became engrossed in what he was teaching, though thoughts of what might happen later were never far off. Class flew by and the next thing you knew, there was only five minutes left.

“All right guys,” he said, grabbing a stack of papers from his desk. “As some of you have heard, I’m looking for a teaching assistant for the semester. I’ve got some applications, if anyone is interested, come grab one from me before you leave.” He waved the papers at the class, then set them on the corner of his desk.

You couldn’t believe the mad rush of students that headed for Dean’s desk, snatching up the applications, crowding him and asking him questions. For a good ten minutes he was surrounded by people, answering questions right and left, smiling and laughing. You hung back, waiting. The room eventually cleared, once everyone had their applications and had asked their questions.

When the door closed behind the last student, Dean walked up the stairs and locked them. You watched him as he casually strolled back down the stairs, loosening his tie as he walked, pulling it off and dropping it on your desk. He took your hand and pulled you to your feet.

“Let’s go make ourselves comfortable on my ugly plaid couch,” he said, pushing you in front of him, his arms sliding around your waist, nuzzling your neck with his nose.

“I hate that couch,” you mumbled, but your thoughts weren’t on the couch, they were on Dean’s hands sliding down your stomach, drifting over the waistband of your shorts and over your bare thighs, and the tiny nips he was placing at the juncture between your neck and shoulder, and his scent surrounding you. Your head fell back against his shoulder and your hands rested lightly on his as he steered you across the classroom and into his office, his lips never straying from your neck.

The inside of his office was still filled with boxes, though it looked like he’d rearranged them, stacking most of them against the far wall. He stopped in front of the ugly plaid couch and you could feel him smiling against your neck as his fingers slid into the waistband of your shorts and he pushed them down, his skin hot against yours. You kicked off your sandals as your shorts fell to the ground.

Dean lightly caressed you, his fingers dancing over your rapidly dampening panties. He slowly lowered you to the couch, lying you on your back, pushing your knees open. He hovered over you, dropping his head to kiss you, one hand sliding past the waistband of your little black panties, pushing them over your legs and off, while his other hand pulled at the bottom of your t-shirt, tugging it up. He rested his hand on the bare skin of your stomach as he explored you, his lips on your neck, mouthing your still clothed breasts, then finally moving down your body to your stomach, covering you in wet, open-mouthed kisses.

You tried to sit up, anxious to get your hands on him, but he took hold of your wrists, holding them at your sides. He continued his trek down your body, his hands now holding yours, his lips moving down your stomach, nipping at your hipbones, his tongue sliding over your upper thighs, the soft hairs of his beard tickling you. You squirmed, trying fruitlessly to free your wrists. He was a lot stronger than you’d realized.

He let go of one of your hands, his own hand now free and sliding up your thigh to slowly caress your slick folds, his tongue licking eagerly at your clit. You gasped and tangled your fingers in his hair, your hips rising to meet his mouth.

“Such an eager student,” he chuckled. He hummed low in the back of his throat as he sucked your clit into his mouth and slowly slipped his finger inside you, pumping it carefully in and out.

You squeezed your eyes closed as Dean gently explored you with his tongue and his fingers. At first, he moved almost lazily, easing you along, tasting, sucking, licking until you were writhing beneath him, begging for more. It seemed to spur him on, because he suddenly released your hand, pulled your legs over his shoulders and buried his head between your legs, his tongue sliding deep inside you alongside his fingers, his thumb pressed against your clit, moving in tight, even circles.

A shot of pure adrenaline burst through you, shattering you into pieces, the orgasm roaring through you. You gripped his shoulders, your nails digging into the tight muscles. He was working you over like a man possessed, possessed with the singular idea of giving you pleasure.

You’d never felt anything like what he was doing to you with just his mouth and his hand. You weren’t a virgin by any means, but the sum total of your previous experiences paled in comparison to the last few minutes with Dean.

When he finally pulled away, you were still gasping and moaning, your body burning with want. “Wow, Professor Winchester,” you murmured. “That was impressive.”

Dean smiled at you, pushing himself to his feet. “I love it when you call me that,” he laughed. He hurriedly unbuttoned his dress shirt, shucking it and his pants off, kicking his dress shoes under the couch. He sat on the edge next to you, his hand on your hip, as he yanked off his socks and pulled something from his wallet. He slipped the foil wrapped packet into your hand, then leaned over you, his kisses needy and insistent. He tugged your t-shirt over your head, his hands sliding around your back to pull off your bra, dropping it to the floor with the rest of the clothes. He moved from your mouth, down your neck and over your chest to your breast, pulling it into his mouth. His tongue danced around the nipple, laving it gently, biting it.

His cock was hard, pressing into your leg. You stroked him, taking your time. He moaned against your breast, his hand sliding between your legs, his fingers easily sliding inside you, immediately setting you on edge. You released him long enough to slide the condom down his shaft and then he was easing himself inside you, his hands on your ass, lifting you to meet him.

You moaned as he filled you, along with an overwhelming sense of rightness, like you weren’t meant to be anywhere else or to be with anyone but him. He moved inside you, the two of you completely in touch with the other’s wants and needs, each moan answered with a quiet sigh or subtle groan. You had one hand on his back, the other thrown over your head, holding onto the arm of the ugly plaid couch as Dean pulled out, then with a long groan slammed back into you. He caught your lips in his, nibbling at them until your mouth opened and his tongue slipped inside, your moans of pleasure mingling with his.

The two of you were a mass of lust, bodies sliding and rubbing against each other, hands touching and caressing, mouths tasting and consuming, nothing left between you but the need to give the other pleasure. You wrapped your legs around the back of his thighs, pulling him into you, your hips rising up to meet his, his thrusts harder, deeper, longer. All of a sudden, it felt like a dam bursting inside you, the heat exploding outward, rushing through your nerve endings, your mind reeling from the force of what you were feeling, what you were experiencing, this orgasm better than the first.

A couple of hard thrusts later and Dean was right behind you, his body tensing as he came with a low moan of your name. He wrapped his arms around you, keeping you nestled close to him, smiling slightly and raining kisses across your face. You smiled up at him, your hand resting on the side of his face. He turned his head and kissed the palm of your hand.

“Still hate my couch, Miss Y/L/N?” he asked.

“Not so much,” you laughed. “I guess it’s not as bad as I thought.”

You and Dean cuddled until your eye caught the time on the clock at the end of his desk. “I have a study group in twenty minutes,” you sighed. “I need to go.” Reluctantly, you managed to separate yourself from him and put your clothes back on. He sat beside you, a hand on your back, rubbing it gently. Once your clothes were on, you handed him his. He stepped into his pants, pulling them on and buttoning and zipping them, but he stopped and pulled you back down onto the couch with him, kissing you again.

“I can’t stop touching you,” he mumbled, his breath hot against the skin of your neck. “Kissing you.” He cupped your cheek in his hand, staring at you. “Are we good? You know, aside from the whole forbidden love affair thing?”

You laughed and kissed him, your hand splayed over his naked chest. “Yeah, we’re good. Like I said, we’ll figure it out.” You kissed him one more time, stood up and slipped on your sandals.

You were halfway across his classroom when you remembered. You crossed the room to his desk, searching until you saw what you were looking for. You picked up one of the teaching assistant applications, stepped into his office and waved it at him. “I’ll get this back to you right away, Professor Winchester!” you yelled over your shoulder as you turned and hurried from the room.

“I love it when you call me that!” you heard him yell as the classroom door swung closed behind you.


End file.
